p-Toluenesulfonic acid → 5,6-dihydro-3-methoxy-12-phenylnaphtho[1,2-b][1,8]naphthyridin-7(12H)-one

HRID 893833Notes

Reaction equation

HRID 893833 reaction equation
COC1C=C2C(=CC=1)C(=O)CCC2.C1(NC2N=CC=CC=2C(OC)=O)C=CC=CC=1.[CH3:31][O:32][C:33]1[CH:34]=[C:35]2[C:40](=[CH:41][CH:42]=1)[C:39](=O)[CH:38]([C:44]([C:46]1[C:47]([NH:52][C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)=[N:48][CH:49]=[CH:50][CH:51]=1)=[O:45])[CH2:37][CH2:36]2.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:31][O:32][C:33]1[CH:42]=[CH:41][C:40]2[C:39]3[N:52]([C:53]4[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=4)[C:47]4[C:46]([C:44](=[O:45])[C:38]=3[CH2:37][CH2:36][C:35]=2[CH:34]=1)=[CH:51][CH:50]=[CH:49][N:48]=4

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 141126-Methoxy-alpha-tetraloneHCID 10998755Methyl 2-anilinopyridine-3-carboxylateHCID 193925563,4-dihydro-6-methoxy-2-[[2-(phenylamino)-3-pyridinyl]-carbonyl]-1(2H)-napthalenone

Product 1

HCID 144232745,6-dihydro-3-methoxy-12-phenylnaphtho[1,2-b][1,8]naphthyridin-7(12H)-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

For example, with 3,4-dihydro-6-methoxy-1-napthalenone as the ketone and methyl 2-phenylaminonicotinate as the arylaminonicotinate, the 1,3-diketone, 3,4-dihydro-6-methoxy-2-[[2-(phenylamino)-3-pyridinyl]carbonyl]-1(2H)-napthalenone, results from the process of Example 8. To cyclize, reflux 9 g of the diketone in 400 ml of toluene containing a catalytic amount of p-toluenesulfonic acid. Collect the evolved water in a Dean-Stark trap. Remove the heat after 21/2 hours and allow the mixture to stand overnight. Distill the toluene under vacuum on a steam bath and crystallize the residue from acetonitrile, to provide the product 5,6-dihydro-3-methoxy-12-phenylnaphtho[1,2-b][1,8]naphthyridin-7(12H)-one, m.p. 234°-237.5° C., after crystallization from CH3CN.

Workup

  1. customCollect the evolved water in a Dean-Stark trap
  2. customRemove the
  3. temperatureheat after 21/2 hours
  4. distillationDistill the toluene under vacuum on a steam bath
  5. customcrystallize the residue from acetonitrile

Sources & evidence

ORD record
ord-bad22cb9e14e492180496b488c211940
Source dataset
uspto-grants-1992_06
Patent number
US05126352

Reaction notes

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